Cyclopentadienyl anion

Identifiers

CAS Number

12127-83-2

3D model (Jmol)

Interactive image

ChemSpider

2731064

PubChem CID

3490527

InChI

InChI=1S/C5H5/c1-2-4-5-3-1/h1-5H/q-1

Key: SINKOGOPEQSHQD-UHFFFAOYSA-N
InChI=1/C5H5/c1-2-4-5-3-1/h1-5H/q-1

Key: SINKOGOPEQSHQD-UHFFFAOYAD

SMILES

[cH-]1cccc1

Properties

Chemical formula

[C₅H₅]⁻ or Cp⁻

Molar mass

65.09 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of [C₅H₅]⁻ and abbreviated as Cp⁻. Its name derives from the molecule cyclopentadiene. Salts of the cyclopentadienyl anion can be stable, e.g., sodium cyclopentadienide. more complex coordination compounds are known as cyclopentadienyl complexes, such as metallocene

It is a regular pentagonal, planar, cyclic ion; as well, it has 6 π-electrons (4n+2, where n=1), which fulfills Hückel's rule of aromaticity. It can coordinate as a ligand to metal atoms.

The structure shown is a composite of five resonance contributors in which each carbon atom carries part of the negative charge.

...
Wikipedia